| | Heat | Dash | B Feature | A Feature |
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| 4/12/2019 | Devil's Bowl Speedway - Mesquite, TX Texas Outlaw Nationals 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 11th |
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| 4/26/2019 | Lake Ozark Speedway - Eldon, MO WORLD OF OUTLAWS SPRINT CARS!!! + POWRI Racesavers, Midwest Lighting Sprints 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged, Lightning Sprints | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 5th | - | 10th |
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| 4/27/2019 | Federated Auto Parts I-55 Raceway - Pevely, MO With the World of Outlaws 410 Sprints - Winged: World of Outlaws Midgets: POWRi National Midgets | Rain Out |
| 4/28/2019 | Jacksonville Speedway - Jacksonville, IL With the World of Outlaws 410 Sprints - Winged: World of Outlaws Midgets: POWRi National Midgets | Results | | Kerry Madsen (410 Sprints - Winged) | - | - | - | - |
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| 5/3/2019 | Riverside International Speedway - West Memphis, AR 410 Sprints - Winged: World of Outlaws Stock Cars, Dirt Late Models | Rain Out |
| 5/4/2019 | Knoxville Raceway - Knoxville, IA 360 Sprints - Winged, 410 Sprints - Winged, 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 3rd | - | - | 2nd |
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| 5/10/2019 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged: USAC National Sprint Cars | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | - | 1st | 19th |
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| 5/10/2019 | Jackson Motorplex - Jackson, MN Casey's Great Lakes Shootout presented by Harvey's Roofing & Tweeter Contracting 410 Sprints - Winged: IRA Interstate Racing Association 305 Sprints - Winged | Postponed |
| 5/17/2019 | Wilmot Raceway - Wilmot, WI 410 Sprints - Winged: IRA Interstate Racing Association with All Star Circuit of Champions Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Rain Out |
| 5/18/2019 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: Midwest Sprint Car Association 410 Sprints - Winged: IRA Interstate Racing Association with All Star Circuit of Champions | Rain Out |
| 5/19/2019 | Angell Park Speedway - Sun Prairie, WI Tony Stewart Sprint Spectacular 410 Sprints - Winged: IRA Interstate Racing Association with All Star Circuit of Champions Badger Midgets: Badger Midget Auto Racing Association Midgets | Rain Out |
| 5/24/2019 | Attica Raceway Park - Attica, OH 410 Sprints - Winged: All Star Circuit of Champions with All Star Circuit 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | - | - | - | - |
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| 5/25/2019 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 1st | - | 3rd |
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| 5/25/2019 | Wayne County Speedway - Orrville, OH 410 Sprints - Winged: All Star Circuit of Champions | Rain Out |
| 5/26/2019 | Fremont Speedway - Fremont, OH 410 Sprints - Winged: All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | - | - | - | - |
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| 5/30/2019 | Mansfield Motor Speedway - Mansfield, OH Sprint Car World Championship 410 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | - | - | - | - |
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| 5/31/2019 | Mansfield Motor Speedway - Mansfield, OH Sprint Car World Championship 410 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | - | - | - | - |
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| 6/1/2019 | Knoxville Raceway - Knoxville, IA 360 Sprints - Winged: Nebraska 360 sprints with Midwest Power Series 410 Sprints - Winged, 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | - | - | 2nd |
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| 6/1/2019 | Mansfield Motor Speedway - Mansfield, OH Sprint Car World Championship 410 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | - | - | - | - |
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| 6/4/2019 | Fairbury Speedway - Fairbury, IL 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | 4th | - | 3rd |
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| 6/7/2019 | River Cities Speedway - Grand Forks, ND 410 Sprints - Winged: World of Outlaws WISSOTA Late Model | Results | | Kerry Madsen (410 Sprints - Winged) | 3rd | - | - | 8th |
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| 6/8/2019 | Granite City Motor Park - Sauk Rapids, MN 410 Sprints - Winged: World of Outlaws Winged A-Class, WISSOTA Super Stock | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 5th | - | 6th |
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| 6/21/2019 | Jackson Motorplex - Jackson, MN Big Country 107.7 Night 360 Sprints - Winged: Midwest Sprint Touring Series with Midwest Power Series 305 Sprints - Winged, 360 Sprints - Non-Winged | Rain Out |
| 6/23/2019 | Dubuque Fairgrounds Speedway - Dubuque, IA 410 Sprints - Winged: World of Outlaws Pro Legends | Rain Out |
| 6/27/2019 | Jackson Motorplex - Jackson, MN 41st annual AGCO Jackson Nationals 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 6th | - | 1st | 13th |
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| 6/28/2019 | Jackson Motorplex - Jackson, MN 41st annual AGCO Jackson Nationals 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 10th (DNF) | - | 10th | - |
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| 6/29/2019 | Jackson Motorplex - Jackson, MN 41st annual AGCO Jackson Nationals 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | 4th | 15th |
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| 7/3/2019 | Brown County Speedway - Aberdeen, SD 410 Sprints - Winged: World of Outlaws Dirt Late Models: Tri-State Late Models Pure Stock | Results | | Kerry Madsen (410 Sprints - Winged) | 6th | - | - | 12th |
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| 7/17/2019 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged: USAC National Sprint Cars | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | - | - | 23rd (DNF) |
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| 7/18/2019 | Eldora Speedway - Rossburg, OH Jokers Wild 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 8th | - | 11th | - |
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| 7/19/2019 | Eldora Speedway - Rossburg, OH The Knight before the Kings Royal 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | - | 1st | 14th |
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| 7/20/2019 | Eldora Speedway - Rossburg, OH 36th Annual Kings Royal 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | - | - | 10th |
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| 7/25/2019 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: Midwest Sprint Car Association 410 Sprints - Winged: IRA Interstate Racing Association with All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | 3rd | - | 9th |
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| 7/26/2019 | Jackson Motorplex - Jackson, MN Tony Stewart Night Presented by C&B Operations 410 Sprints - Winged: All Star Circuit of Champions 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 4th |
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| 7/27/2019 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: All Star Circuit of Champions 360 Sprints - Winged, 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | 1st | - | 2nd |
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| 7/28/2019 | 34 Raceway - West Burlington, IA 410 Sprints - Winged: All Star Circuit of Champions Stock Cars, 2WD Trucks | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | - | - | 12th |
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| 8/2/2019 | Federated Auto Parts I-55 Raceway - Pevely, MO Iron Man 55 410 Sprints - Winged: World of Outlaws Midgets: POWRi National Midgets with POWRi West Midgets | Results | | Kerry Madsen (410 Sprints - Winged) | 6th | - | - | 10th |
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| 8/3/2019 | Federated Auto Parts I-55 Raceway - Pevely, MO Iron Man 55 410 Sprints - Winged: World of Outlaws Midgets: POWRi National Midgets with POWRi West Midgets DIRTcar UMP Modifieds | Results | | Kerry Madsen (410 Sprints - Winged) | 6th | - | - | 12th |
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| 8/7/2019 | Knoxville Raceway - Knoxville, IA Knoxville Nationals 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | 7th | - |
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| 8/9/2019 | Knoxville Raceway - Knoxville, IA Knoxville Nationals 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | - | - | 1st |
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| 8/10/2019 | Knoxville Raceway - Knoxville, IA Knoxville Nationals 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | - | - | - | 11th |
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| 8/16/2019 | River Cities Speedway - Grand Forks, ND 410 Sprints - Winged: World of Outlaws WISSOTA Late Model | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 15th |
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| 9/5/2019 | Bedford Speedway - Bedford, PA $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 6th | - | 9th |
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| 9/6/2019 | Port Royal Speedway - Port Royal, PA Night Before the 50 $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | 3rd | - | 20th (DNF) |
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| 9/7/2019 | Port Royal Speedway - Port Royal, PA 52nd Annual Tuscarora 50 $52,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | - | - | 27th |
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| 9/20/2019 | Williams Grove Speedway - Mechanicsburg, PA The Tommy Hinnershitz Memorial $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions 358 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 4th | - | 6th |
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| 9/21/2019 | Lincoln Speedway - Abbottstown, PA The Dirt Classic $20,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | - | - | 10th |
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| 9/22/2019 | Hagerstown Speedway - Hagerstown, MD $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | - | - | 16th |
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| 9/27/2019 | Eldora Speedway - Rossburg, OH BeFour the Crowns Showdown 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 6th | - | 4th |
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| 9/28/2019 | Lernerville Speedway - Sarver, PA Commonwealth Clash 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged: Allegheny Sprint Tour | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 12th |
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| 10/4/2019 | Williams Grove Speedway - Mechanicsburg, PA National Open 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | - | 3rd | 30th |
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| 10/5/2019 | Williams Grove Speedway - Mechanicsburg, PA National Open 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | 5th | - | 11th |
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| 10/13/2019 | Tri-State Speedway - Haubstadt, IN 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | 4th | - | 3rd |
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| 10/19/2019 | Lake Ozark Speedway - Eldon, MO Jason Johnson Classic / World Of Outlaws ! Invades For 2nd Time In 2019! 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 6th | - | - | 11th |
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| 10/25/2019 | Port Royal Speedway - Port Royal, PA 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | - | - | - | - |
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| 11/8/2019 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Kerry Madsen (410 Sprints - Winged) | 3rd | - | - | 8th |
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| 11/9/2019 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Kerry Madsen (410 Sprints - Winged) | 3rd | - | - | 21st (DNF) |
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| 12/26/2019 | Murray Bridge Speedway - Murray Bridge, SA World Series Sprint Cars 410 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 7th | - | - | 2nd |
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| 12/27/2019 | Murray Bridge Speedway - Murray Bridge, SA World Series Sprint Cars 410 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | 3rd | - | 2nd |
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